We intend to deepen the understanding of leadership in general and educational leadership in particular by an analysis of Chester Barnard's (1938) concept of executive responsibility. By so doing we believe that we will reveal how an educational leader can foster the environment in which competent teachers can optimize their students' learning experience. We will contend that Barnard's (1938) theory of executive leadership and organizational effectiveness would have dealt much better with the dilemmas of "Billy Budd" than either Rand (1957) or Gomba (2012) and by extension would deal much better with the kind of organization either would suited to their models.